1-Iodopentane → 2,2,2-trifluoro-N-pentyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2,2-trifluoro-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (29) (15.05 g, 40.7 mmole) in 105 mL dimethylsulfoxide (DMSO) was treated with potassium hydroxide (3.38 g) and then cooled to 0° C. Iodopentane (7.9 mL) in 15 mL DMSO was added dropwise to the reaction mixture and the temperature was allowed to rise to 23° C. The reaction mixture was stirred at room temperature for 24 hours, diluted with 200 mL of water and extracted with two 200 mL portions of ether. The combined organic extracts were washed with four 200 mL portions of cold water, dried over MgSO4, filtered and concentrated in vacuo to give a brown oil. The product was purified by flash chromatography (SiO2, 1:15 ethyl acetate/hexanes) to afford 14.36 g of 2,2,2-trifluoro-N-pentyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (31) as a pale yellow oil.

Provenance & Evidence